Methyl D-valinate hydrochloride → (R)-Methyl 3-methyl-2-(6-(4-nitrophenyl)-1-oxoisoindolin-2-yl)butanoate

HRID 404053

Reaction equation

HRID 404053 reaction equation
[CH3:1][CH:2]([CH3:27])[C@H:3]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][C:12]([C:17]3[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=3)=[CH:13][CH:14]=2)[C:9]1=[O:26])[C:4]([O:6][CH3:7])=[O:5].BrCC1C=CC(C2C=CC([N+]([O-])=O)=CC=2)=CC=1C(OC)=O.Cl.COC(=O)[C@@H](C(C)C)N>>[CH3:1][CH:2]([CH3:27])[C@@H:3]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][C:12]([C:17]3[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=3)=[CH:13][CH:14]=2)[C:9]1=[O:26])[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 3

HCID 11984198Methyl D-valinate hydrochlorideHCID 67306641Methyl 4-(bromomethyl)-4'-nitrobiphenyl-3-carboxylateHCID 131731440(S)-Methyl 3-methyl-2-(6-(4-nitrophenyl)-1-oxoisoindolin-2-yl)butanoate

Product 1

HCID 131731581(R)-Methyl 3-methyl-2-(6-(4-nitrophenyl)-1-oxoisoindolin-2-yl)butanoateYield 77%

Procedure

The compound of example 538 was prepared analogous to compound of example 5 by reaction of compound of example 4 with D-valine methyl ester hydrochloride.

Sources & evidence

ORD record
ord-9d2438bd1233441db0ab6d10395d4eda
Source dataset
uspto-grants-2014_06
Patent number
US08748426B2

Linked notes

Loading…